FI84906B - Koncentrerade loesningar av dinitrofenoler som aer stabila vid laoga temperaturer. - Google Patents
Koncentrerade loesningar av dinitrofenoler som aer stabila vid laoga temperaturer. Download PDFInfo
- Publication number
- FI84906B FI84906B FI870071A FI870071A FI84906B FI 84906 B FI84906 B FI 84906B FI 870071 A FI870071 A FI 870071A FI 870071 A FI870071 A FI 870071A FI 84906 B FI84906 B FI 84906B
- Authority
- FI
- Finland
- Prior art keywords
- phenylenediamine
- dinitrophenol
- composition according
- dinitro
- phenyl
- Prior art date
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- 239000002904 solvent Substances 0.000 claims description 39
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 36
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 25
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 24
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- HOYRZHJJAHRMLL-UHFFFAOYSA-N 2,6-dinitro-p-cresol Chemical compound CC1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 HOYRZHJJAHRMLL-UHFFFAOYSA-N 0.000 claims description 18
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 12
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000004986 phenylenediamines Chemical class 0.000 claims description 5
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 5
- PWNBRRGFUVBTQG-UHFFFAOYSA-N 1-n,4-n-di(propan-2-yl)benzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(NC(C)C)C=C1 PWNBRRGFUVBTQG-UHFFFAOYSA-N 0.000 claims description 4
- HBYHYLBZPLCIEE-UHFFFAOYSA-N 2,4-dinitro-6-propan-2-ylphenol Chemical compound CC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O HBYHYLBZPLCIEE-UHFFFAOYSA-N 0.000 claims description 4
- OZOWWGISLRIWQI-UHFFFAOYSA-N 4-n-(4-methylhexan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)CC)=CC=C1NC1=CC=CC=C1 OZOWWGISLRIWQI-UHFFFAOYSA-N 0.000 claims description 4
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- FVMCLNZPDUOPJC-UHFFFAOYSA-N 2,6-dinitro-4-propan-2-ylphenol Chemical compound CC(C)C1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 FVMCLNZPDUOPJC-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 claims 2
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 claims 2
- MDDXGELKFXXQDP-UHFFFAOYSA-N 4-n-(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(N)C=C1 MDDXGELKFXXQDP-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 10
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MGUHTGHCUOCIGG-UHFFFAOYSA-N 1,3-dinitroimidazolidine Chemical compound [O-][N+](=O)N1CCN([N+]([O-])=O)C1 MGUHTGHCUOCIGG-UHFFFAOYSA-N 0.000 description 1
- ZJNLYGOUHDJHMG-UHFFFAOYSA-N 1-n,4-n-bis(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(NC(C)CCC(C)C)C=C1 ZJNLYGOUHDJHMG-UHFFFAOYSA-N 0.000 description 1
- JCRIDWXIBSEOEG-UHFFFAOYSA-N 2,6-dinitrophenol Chemical class OC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O JCRIDWXIBSEOEG-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- -1 aromatic vinyl compound Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/32—Compounds containing nitrogen bound to oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C205/23—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having two nitro groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Claims (17)
1. Vätskekomposition, kännetecknad av att den innehäl- ler en dinitrofenol med följande formel: N02 R1 —^- °H R väri den ena av grupperna R och R* är nitro och den andra är vald ur gruppen som bestär av väte, klor och - Cg -alkyl, upplöst i ett aromatiskt kolvätelösningsmedel, vilken vätskekomposition ytterligare innehäller en tillräcklig mängd av en fenylendiamin med följande formel R2 - NH-^Q^-NH - R3 väri R2 och R3 vardera oberoende av varandra är valda ur gruppen som innefattar väte, Cj - C^2 -alkyl, fenyl och fenyl, som är substituerad med - Cg -alkyl, sä att mängden dinitrofenol som är upplöst i detta lösnings-medel är större än den mängd dinitrofenol som skulle kunna 14 84906 upplösas i detta lösningsmedel ifall denna fenylendiamin ej vore närvarande.
2. Komposition enligt patentkravet 1, kännetecknad av att denna dinitrofenol är vald ur gruppen som bestär av 2,6-dinitro-p-kresol, 4,6-dinitro-o-kresol, 2,6-dinitro-p-isopropylfenol, 4,6-dinitro-o-isopropylfenol och 4,6-di-nitro-o-sek-butylfenol.
3. Komposition enligt patentkravet 1, kännetecknad av att denna fenylendiamin är vald ur gruppen som bestär av N-fenyl-N'-isopropyl-p-fenylendiamin, N-fenyl-N'-(1,3-dime-tylbutyl)-p-fenylendiamin, N-fenyl-N'-(1,3-dimetylpentyl)-p-fenylendiamin, N,N'-di-isopropyl-p-fenylendiamin, N,N'-di-sek-butyl-p-fenylendiamin och N,N'-bis(1,4-dimetylpen-tyl)-p-fenylendiamin, .
4. Komposition enligt patentkravet 1, kännetecknad av nämnda aromatiska kolvätelösningsmedel är valt ur gruppen som bestär av bensen, toluen, xylen, etylbensen, styren, vinyltoluen, divinylbensen och alfa-metylstyren.
5. Komposition enligt patentkravet 4, kännetecknad av att nämnda aromatiska kolväte är valt ur gruppen som bestär av styren och etylbensen.
6. Komposition enligt patentkravet 1, kännetecknad av att viktförhällandet mellan dinitrofenol + fenylendiamin och aromatiskt kolvätelösningsmedel är mellan cirka 1:4 och cirka 2:1.
7. Komposition enligt patentkravet 1, kännetecknad av att viktförhällandet mellan dinitrofenol och fenylendiamin är mellan cirka 2:3 och 3:2.
8. Komposition enligt patentkravet 1, kännetecknad av att viktförhällandet mellan dinitrofenol och fenylendiamin är mellan cirka 1:9 och cirka 9:1, och att viktförhällandet i: 15 84906 mellan dinitrofenol + fenylendiamin och aromatiskt kolväte-lösningsmedel är ätminstone cirka 1:10.
9. Komposition enligt patentkravet 8, kännetecknad av att nämnda dinitrofenol är vald ur gruppen som bestär av 2,6-dinitro-p-kresol, 4,6-dinitro-o-kresol, 2,6-dinitro-p-isopropylfenol, 4,6-dinitro-o-isopropylfenol och 4,6-di-nitro-o-sek-butylfenol.
10. Komposition enligt patentkravet 8, kännetecknad av att nämnda fenylendiamin är vald ur gruppen som bestär av N-fenyl-N'-isopropyl-p-fenylen-diamin, N-fenyl-N'-(1,3-di-metylbutyl)-p-fenylendiamin, N-fenyl-N'-(1,3-dimetylpentyl)-p-fenylendiamin, N,N'-diisopropyl-p-fenylendiamin, N,N'-di-sek-butyl-p-fenylendiamin och N,N'-bis(1,4-dimetylpen-tyl)-p-fenylendiamin.
11. Komposition enligt patentkravet 8, kännetecknad av att nämnda aromatiska kolvätelösningsmedel är valt ur gruppen som bestär av bensen, toluen, xylen, etylbensen, sty-ren, vinyltoluen, divinylbensen och alfa-metylstyren.
12. Komposition enligt patentkravet 8, kännetecknad av att nämnda aromatiska kolväte är valt ur gruppen som bestär av styren och etylbensen.
13. Komposition enligt patentkravet 8, kännetecknad av att viktförhällandet mellan dinitrofenol + fenylendiamin och aromatiskt kolvätelösningsmedel är mellan cirka 1:4 och 2:1.
14. Komposition enligt patentkravet 8, kännetecknad av att viktförhällandet mellan dinitrofenol och fenylendiamin är mellan cirka 2:3 och 3:2.
15. Komposition enligt patentkravet 8, kännetecknad av att nämnda dinitrofenol är vald ur gruppen som bestär av 16 84906 2,6-dinitro-p-kresol, 4,6-dinitro-o-isopropylfenol och 4,6-dinitro-o-sek-butylfenol; att nämnda fenylendiamin är vald ur gruppen som bestir av N-fenyl-N'-isopropyl-p-fenylen-diamin, N-fenyl-N'-(1,3-dimetylbutyl)-p-fenylendiamin, N-fenyl-N'-(1,3-dimetylpentyl)-p-fenylendiamin. N,N'-diiso-propyl-p-fenylendiamin, N,Ν'-bis(1,4-dimetylpentyl)-p-fenylendiamin; och att nämnda aromatiska kolvätelösningsmedel är valt ur gruppen som bestär av bensen, toluen, xylen, etylbensen, styren, vinyltoluen, divinylbensen och alfa-metylstyren.
16. Komposition enligt patentkravet 15, kännetecknad av att viktförhillandet mellan dinitrofenol + fenylendiamin och aromatiskt kolvätelösningsmedel är mellan cirka 1:4 och cirka 2:1.
17. Komposition enligt patentkravet 15, kännetecknad av att viktförhillandet mellan dinitrofenol och fenylendiamin är mellan cirka 2:3 och 3:2.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81732486 | 1986-01-09 | ||
| US06/817,324 US4664845A (en) | 1986-01-09 | 1986-01-09 | Phenylenediamine solubilizer for dinitrophenol in aromatic solvent |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI870071A0 FI870071A0 (fi) | 1987-01-08 |
| FI870071A FI870071A (fi) | 1987-07-10 |
| FI84906B true FI84906B (fi) | 1991-10-31 |
| FI84906C FI84906C (sv) | 1992-02-10 |
Family
ID=25222823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI870071A FI84906C (sv) | 1986-01-09 | 1987-01-08 | Koncentrerade lösningar av dinitrofenoler som är stabila vid låga temp eraturer |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4664845A (sv) |
| EP (1) | EP0234671B1 (sv) |
| JP (1) | JPH01152146A (sv) |
| KR (1) | KR910004552B1 (sv) |
| CN (1) | CN1004139B (sv) |
| AR (1) | AR245096A1 (sv) |
| AT (1) | ATE63534T1 (sv) |
| AU (1) | AU595571B2 (sv) |
| BR (1) | BR8700050A (sv) |
| CA (1) | CA1275168C (sv) |
| DE (1) | DE3770019D1 (sv) |
| DK (1) | DK11387A (sv) |
| ES (1) | ES2022880B3 (sv) |
| FI (1) | FI84906C (sv) |
| IN (1) | IN166453B (sv) |
| MX (1) | MX165080B (sv) |
| PT (1) | PT84086B (sv) |
| ZA (1) | ZA8769B (sv) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4774374A (en) * | 1987-06-12 | 1988-09-27 | Uniroyal Chemical Company, Inc. | Stabilized vinyl aromatic composition |
| US4915873A (en) * | 1988-01-22 | 1990-04-10 | Uniroyal Chemical Company, Inc. | Polymerization inhibitor composition for vinyl aromatic compounds |
| DE3825163A1 (de) * | 1988-07-23 | 1990-02-01 | Wella Ag | Verwendung von 2,6-dinitro-phenol-derivaten in haarfaerbemitteln |
| US5312952A (en) * | 1992-04-23 | 1994-05-17 | Uniroyal Chemical Company, Inc. | Polymerization inhibitor for vinyl aromatics |
| US5254760A (en) * | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
| US5332842A (en) * | 1993-05-13 | 1994-07-26 | Exxon Chemical Patents Inc. | Process for inhibiting oxidation and polymerization of furfural and its derivatives |
| US6344560B1 (en) | 2000-05-03 | 2002-02-05 | Uniroyal Chemical Company, Inc. | Nitroaromatic solubilizer for nitroxyls in aromatic solvents |
| US6339177B1 (en) * | 2000-05-24 | 2002-01-15 | Sea Lion Technology, Inc. | Dinitroalkyl aromatics polymerization retarders or inhibitors and methods for making and for using same |
| US20060069219A1 (en) * | 2004-09-28 | 2006-03-30 | Vilan Kosover | Sulfonated phenols with nitrophenols as polymerization inhibitors |
| US8098683B2 (en) * | 2004-10-06 | 2012-01-17 | Broadcom Corporation | Method and system for implementing a single weight (SW) single channel (SC) MIMO system with no insertion loss |
| WO2006051941A1 (ja) * | 2004-11-15 | 2006-05-18 | Hakuto Co., Ltd. | ジビニルベンゼンと芳香族ビニル化合物を含む共重合体の重合抑制方法 |
| US7696290B2 (en) * | 2004-12-03 | 2010-04-13 | Crompton Corporation | Aromatic sulfonic acids, amines, and nitrophenols in combination with nitroxyl radical-containing compounds or C-nitrosanilines as polymerization inhibitors |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB504765A (en) * | 1937-12-24 | 1939-05-01 | Standard Telephones Cables Ltd | Improvements in or relating to the stabilisation of styrene |
| US2526567A (en) * | 1948-07-06 | 1950-10-17 | Dow Chemical Co | Stabilization of nuclear chlorostyrenes by 2, 6-dinitrophenols |
| US2943075A (en) * | 1956-07-02 | 1960-06-28 | Dow Chemical Co | Styrene-modified rubbery compositions and stabilized with 2-nitrophenols |
| US3366702A (en) * | 1965-05-03 | 1968-01-30 | Marathon Oil Co | Preparation of unsaturated hydrocarbons by pyrolysis, and related compositions |
| US3420778A (en) * | 1966-07-21 | 1969-01-07 | Simplex Wire & Cable Co | Voltage stabilized liquid dielectrics |
| FR2142369A5 (sv) * | 1971-06-18 | 1973-01-26 | Huels Chemische Werke Ag | |
| US4051067A (en) * | 1974-01-25 | 1977-09-27 | Monsanto Company | Stabilization of unsaturated carboxylic acid esters with mixtures of polyalkyleneamines and arylenediamines |
| US4105506A (en) * | 1977-02-24 | 1978-08-08 | Cosden Technology, Inc. | Polymerization inhibitor for vinyl aromatic compounds |
| US4132603A (en) * | 1977-11-23 | 1979-01-02 | Cosden Technology, Inc. | Polymerization inhibitor for vinyl aromatic compounds |
| BE875237R (fr) * | 1978-07-18 | 1979-07-16 | Cosden Technology | Procede pour inhiber la polymerisation de composes vinylaromatiques facilement polymerisables |
| US4376221A (en) * | 1980-03-13 | 1983-03-08 | Jackisch Philip F | Stabilization of dibromostyrene |
| US4457806A (en) * | 1982-06-28 | 1984-07-03 | The Sherwin-Williams Company | Process for vinyl aromatic monomer polymerization inhibition |
| US4466905A (en) * | 1983-04-11 | 1984-08-21 | Cosden Technology, Inc. | Polymerization inhibition process for vinyl aromatic compounds |
| US4468343A (en) * | 1983-04-11 | 1984-08-28 | Cosden Technology, Inc. | Polymerization co-inhibitors for vinyl aromatic compounds |
| US4568711A (en) * | 1984-12-07 | 1986-02-04 | The Firestone Tire & Rubber Company | Synergistic additive combination for guayule rubber stabilization |
| US4654451A (en) * | 1985-12-27 | 1987-03-31 | Atlantic Richfield Company | Inhibiting polymerization of vinyl aromatic monomers |
-
1986
- 1986-01-09 US US06/817,324 patent/US4664845A/en not_active Expired - Lifetime
- 1986-03-07 IN IN212/DEL/86A patent/IN166453B/en unknown
-
1987
- 1987-01-06 ES ES87300037T patent/ES2022880B3/es not_active Expired - Lifetime
- 1987-01-06 EP EP87300037A patent/EP0234671B1/en not_active Expired - Lifetime
- 1987-01-06 AT AT87300037T patent/ATE63534T1/de not_active IP Right Cessation
- 1987-01-06 AU AU67177/87A patent/AU595571B2/en not_active Ceased
- 1987-01-06 ZA ZA8769A patent/ZA8769B/xx unknown
- 1987-01-06 DE DE8787300037T patent/DE3770019D1/de not_active Expired - Fee Related
- 1987-01-07 CA CA000526832A patent/CA1275168C/en not_active Expired - Fee Related
- 1987-01-08 KR KR1019870000065A patent/KR910004552B1/ko not_active IP Right Cessation
- 1987-01-08 BR BR8700050A patent/BR8700050A/pt not_active IP Right Cessation
- 1987-01-08 FI FI870071A patent/FI84906C/sv not_active IP Right Cessation
- 1987-01-08 CN CN87100819.XA patent/CN1004139B/zh not_active Expired
- 1987-01-09 JP JP62003094A patent/JPH01152146A/ja active Granted
- 1987-01-09 PT PT84086A patent/PT84086B/pt not_active IP Right Cessation
- 1987-01-09 MX MX4906A patent/MX165080B/es unknown
- 1987-01-09 DK DK011387A patent/DK11387A/da not_active Application Discontinuation
- 1987-01-09 AR AR87306440A patent/AR245096A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AR245096A1 (es) | 1993-12-30 |
| KR870007227A (ko) | 1987-08-17 |
| FI84906C (sv) | 1992-02-10 |
| AU6717787A (en) | 1987-07-16 |
| KR910004552B1 (ko) | 1991-07-06 |
| CN1004139B (zh) | 1989-05-10 |
| EP0234671B1 (en) | 1991-05-15 |
| FI870071A (fi) | 1987-07-10 |
| DK11387A (da) | 1987-07-10 |
| JPH0588699B2 (sv) | 1993-12-24 |
| CN87100819A (zh) | 1987-09-23 |
| CA1275168C (en) | 1990-10-16 |
| ZA8769B (en) | 1987-08-26 |
| DE3770019D1 (de) | 1991-06-20 |
| PT84086A (en) | 1987-02-01 |
| BR8700050A (pt) | 1987-12-01 |
| IN166453B (sv) | 1990-05-12 |
| EP0234671A1 (en) | 1987-09-02 |
| MX165080B (es) | 1992-10-21 |
| PT84086B (pt) | 1989-02-28 |
| JPH01152146A (ja) | 1989-06-14 |
| FI870071A0 (fi) | 1987-01-08 |
| ATE63534T1 (de) | 1991-06-15 |
| DK11387D0 (da) | 1987-01-09 |
| US4664845A (en) | 1987-05-12 |
| AU595571B2 (en) | 1990-04-05 |
| ES2022880B3 (es) | 1991-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: UNIROYAL CHEMICAL COMPANY, INC. |